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Name	Tacalcitol	EINECS	N/A
CAS No.	57333-96-7	Density	1.06 g/cm³
PSA	60.69000	LogP	5.56060
Solubility	N/A	Melting Point	N/A
Formula	C₂₇H₄₄O₃	Boiling Point	565 °C at 760 mmHg
Molecular Weight	416.645	Flash Point	238.4 °C
Transport Information	N/A	Appearance	N/A
Safety		Risk Codes	R50/53; R33; R26/27/28
Molecular Structure		Hazard Symbols	N,T+
Synonyms	1a,24R-Dihydroxyvitamin D3;Bonalfa;Curatoderm;PRI 2191;TV 02;9,10-Secocholesta-5,7,10(19)-triene-1,3,24-triol,(1a,3b,5Z,7E,24R)- (9CI);1a,24(R)-Dihydroxycholecalciferol;	Article Data	9

Tacalcitol Synthetic route

: ((1R,3S,Z)-5-((E)-2-((1R,7aR)-7a-methyl-1((2R,5R)-6-methyl-5-(triethylsilyloxy)heptan-2-yl)dihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

: 57333-96-7
tacalcitol

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; Darkness;	98%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 40h; Darkness;	98%

: (1R,3S)-5-[2-[(1R,3aS,7aR)-1-((1R,4R)-4-Methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexane-1,3-diol

: 57333-96-7
tacalcitol

Conditions

Conditions	Yield
With hydrogen fluoride In water; acetonitrile at 20℃; for 24h;	76%
With methanol; AG 50W-X4 resin at 20℃; methanolysis;	33 mg

: C41H74O4Si2

: 57333-96-7
tacalcitol

Conditions

Conditions	Yield
Stage #1: C41H74O4Si2 With potassium carbonate In methanol at 20℃; for 5h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Reflux;	75%

: C46H76O4Si2

: 57333-96-7
tacalcitol

Conditions

Conditions	Yield
Stage #1: C46H76O4Si2 With potassium carbonate In methanol at 20℃; for 5h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Reflux;	75%

: C39H72O3Si2

: 57333-96-7
tacalcitol

Conditions

Conditions	Yield
With (1S)-10-camphorsulfonic acid In methanol; chloroform at 20℃; for 2.5h;	65%
Stage #1: C39H72O3Si2 With tetrabutyl ammonium fluoride In tetrahydrofuran at 50 - 55℃; for 2h; Stage #2: With maleic anhydride In ethyl acetate at 30 - 35℃; for 24h;	300 mg

: 57701-47-0
1α,3β,24(R)-trihydroxycholesta-5,7-diene

: 57333-96-7
tacalcitol

Conditions

Conditions	Yield
In diethyl ether Irradiation;

: 66774-80-9
(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate

: 57333-96-7
tacalcitol

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: 91 percent / dimethylsulfoxide / 2 h / 90 °C 2.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C 3.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C 3.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C 4.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C 5.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C 6.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating 7.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C 8.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C 8.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C 9.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C 10.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h 11.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating 12.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 13.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C View Scheme

Yield

Multi-step reaction with 13 steps
1.1: 91 percent / dimethylsulfoxide / 2 h / 90 °C
2.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C
3.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
3.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C
4.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
5.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
6.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
7.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
8.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
8.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
9.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
10.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
11.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
12.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
13.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme

: 64190-52-9
(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

: 57333-96-7
tacalcitol

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1.1: 93 percent / pyridine / 12 h / 0 °C 2.1: 91 percent / dimethylsulfoxide / 2 h / 90 °C 3.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C 4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C 4.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C 5.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C 6.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C 7.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating 8.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C 9.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C 9.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C 10.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C 11.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h 12.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating 13.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 14.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C View Scheme
Multi-step reaction with 11 steps 1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 96 h / 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C 3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 0 - 20 °C 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C 5: lithium hexamethyldisilazane / tetrahydrofuran / 15 h / -78 - 20 °C 6: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 65 °C 7: hydrogen; palladium 10% on activated carbon / methanol / 15 h 8: dipyridinium dichromate / dichloromethane / 20 °C 9: n-butyllithium / tetrahydrofuran / 18 h / -78 °C 10: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness 11: hydrogen fluoride / acetonitrile; water / 24 h / 20 °C View Scheme
Multi-step reaction with 10 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 50 - 55 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / -5 - 5 °C 3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / 0.17 h / -5 - 5 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -70 - -60 °C 4.2: -70 - 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 55 - 60 °C 6.1: pyridinium chlorochromate / dichloromethane / 20 °C 7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 24 h / 2280.15 - 2660.18 Torr 8.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C 9.1: n-butyllithium / tetrahydrofuran / 1 h / -70 - -60 °C 9.2: 1.5 h / -65 - -10 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness View Scheme
Multi-step reaction with 10 steps 1.1: 1H-imidazole; ammonium chloride / N,N-dimethyl-formamide / 50 - 55 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -70 °C / Inert atmosphere 4.2: -70 - 20 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 60 °C / Inert atmosphere 6.1: dipyridinium dichromate / dichloromethane / 20 °C 7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 24 h / 2280.15 - 2660.18 Torr 8.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 9.1: n-butyllithium / tetrahydrofuran / 1 h / -65 °C / Inert atmosphere 9.2: 1.5 h / -65 - -10 °C / Inert atmosphere 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 h / 20 °C / Darkness View Scheme

: 93489-60-2
<1R-<1β(R*),3aα,4β,7aβ>>-octahydro-4-hydroxy-β,7a-dimethyl-1H-indene-1-propanenitrile

: 57333-96-7
tacalcitol

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C 2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C 2.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C 3.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C 4.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C 5.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating 6.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C 7.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C 7.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C 8.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C 9.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h 10.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating 11.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 12.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C View Scheme

Yield

Multi-step reaction with 12 steps
1.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C
2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
2.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C
3.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
4.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
5.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
6.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
7.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
7.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
8.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
9.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
10.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
11.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
12.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme

: 145223-31-0
De-A,B-(24R)-8β-[(tert-butyldimethylsilyl)oxy]-cholestan-24-ol

: 57333-96-7
tacalcitol

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C 2.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating 3.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C 4.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C 4.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C 6.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h 7.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating 8.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 9.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
2.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
3.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
4.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
4.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
5.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
6.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
7.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
8.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
9.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme

Tacalcitol Specification

1. Introduction of Tacalcitol

Tacalcitol, with the IUPAC Name of (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,5S)-5-Hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol, is one kind of powder. And it belongs to the Product categories which include Vitamin D3 analogs.

2. Properties of Tacalcitol

Tacalcitol has the following properties: (1)Density: 1.06 g/cm³; (2)Flash Point: 238.4 °C; (3)Index of Refraction: 1.545; (4)Boiling Point: 565 °C at 760 mmHg; (5)Vapour Pressure: 4.05E-15 mmHg at 25°C; (6)Appearance: White solid; (7)Index of Refraction: 1.545; (8)Molar Refractivity: 124.3 cm3; (9)Molar Volume: 392.7 cm3.

3. Structure Descriptors of Tacalcitol

You could convert the following datas into the molecular structure:
(1).Canonical SMILES: CC(C)C(CCC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C)O
(2).Isomeric SMILES: C[C@H](CC[C@@H](C(C)C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C
[C@@H](C3=C)O)O)C
(3).InChI: InChI=1S/C27H44O3/c1-17(2)25(29)13-8-18(3)23-11-12-24-20(7-6-14-27(23,24)5)9-10-21-15-22(28)16-26(30)19(21)4/h9-10,17-18,22-26,28-30H,4,6-8,11-16H2,1-3,5H3/b20-9+,21-10-/t18-,22-,23-,24+,25+,26+,27-/m1/s1
(4).InChIKey: BJYLYJCXYAMOFT-SEZLTJOTSA-N

4. Toxicity of Tacalcitol

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	subcutaneous	10ug/kg (0.01mg/kg)	BEHAVIORAL: FOOD INTAKE (ANIMAL) BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
mouse	LD50	intravenous	559ug/kg (0.559mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
mouse	LD50	oral	3050ug/kg (3.05mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
mouse	LD50	subcutaneous	419ug/kg (0.419mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
rat	LD50	intravenous	556ug/kg (0.556mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
rat	LD50	oral	3279ug/kg (3.279mg/kg)	SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
rat	LD50	subcutaneous	100ug/kg (0.1mg/kg)		Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.
rat	LD50	subcutaneous	100ug/kg (0.1mg/kg)	SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989.

5. Safety Information of Tacalcitol

A poison by ingestion, subcutaneous, and intravenous routes. When heated to decomposition it emits acrid smoke and irritating vapors.

6. Use of Tacalcitol

Tacalcitol (CAS NO.57333-96-7) is a durg for preventing anti-psoriasis and keratosis. It can be used for psoriasis, ichthyosis, palmoplantar keratoderma pus blisters disease and keratosis.

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